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                                                                    EXHIBIT 4.14

              AMENDMENT NO. 1 TO THE 9% CONVERTIBLE DEBENTURE, DUE
           MAY 15, 2006 ISSUED TO MIDSUMMER INVESTMENT LTD. AND WAIVER

         This Amendment No. 1 ("AMENDMENT") is made to that certain 9%
Convertible Debenture, due May 15, 2006 issued by Island Pacific, Inc. (the
"Company") to Midsummer Investment Ltd. ("MIDSUMMER") (the "DEBENTURE") pursuant
to the Securities Purchase Agreement ("PURCHASE AGREEMENT") dated as of March
15, 2004 among the Company, Midsummer and the other purchasers identified on the
signature pages thereto (the "PURCHASERS"). The parties hereto agree as follows:

1.       INTEREST PAYMENTS. The Preamble to the Debenture shall be amended and
         restated as follows:

         FOR VALUE RECEIVED, the Company promises to pay to Midsummer or its
registered assigns (the "HOLDER"), the principal sum of $1,250,000 on May 15,
2006 or such earlier date as the Debentures are required or permitted to be
repaid as provided hereunder (the "MATURITY DATE") and to pay interest to the
Holder on the aggregate unconverted and then outstanding principal amount of
this Debenture at the rate of 9% per annum, payable monthly, beginning on the
first day of the first month after the Original Issue Date and on each
Conversion Date (as to that principal amount then being converted), on each
Monthly Redemption Date (as to that principal amount then being redeemed) and on
the Maturity Date (except that, if any such date is not a Business Day, then
such payment shall be due on the next succeeding Business Day) (each such date,
an "INTEREST PAYMENT DATE"), in cash or shares of Common Stock at the Interest
Conversion Rate, or a combination thereof; PROVIDED, HOWEVER, payment in shares
of Common Stock may only occur if during the 20 Trading Days immediately prior
to the applicable Interest Payment Date all of the Equity Conditions have been
met and the Company shall have given the Holder notice in accordance with the
notice requirements set forth below. Subject to the terms and conditions herein,
the decision whether to pay interest hereunder in shares of Common Stock or cash
shall be at the discretion of the Company. Not less than 20 Trading Days prior
to each Interest Payment Date, the Company shall provide the Holder with written
notice of its election to pay interest hereunder either in cash or shares of
Common Stock (the Company may indicate in such notice that the election
contained in such notice shall continue for later periods until revised). Within
20 Trading Days prior to an Interest Payment Date, the Company's election
(whether specific to an Interest Payment Date or continuous) shall be
irrevocable as to such Interest Payment Date. Subject to the aforementioned
conditions, failure to timely provide such written notice shall be deemed an
election by the Company to pay the interest on such Interest Payment Date in
cash. Interest shall be calculated on the basis of a 360-day year and shall
accrue daily commencing on the Original Issue Date until payment in full of the
principal sum, together with all accrued and unpaid interest and other amounts
which may become due hereunder, has been made. Payment of interest in shares of
Common Stock shall otherwise occur pursuant to Section 4(b) and for purposes of
the payment of interest in shares only, the Interest Payment Date shall be

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deemed the Conversion Date. Interest shall cease to accrue with respect to any
principal amount converted, provided that the Company in fact delivers the
Conversion Shares within the time period required by Section 4(b)(i). Interest
hereunder will be paid to the Person in whose name this Debenture is registered
on the records of the Company regarding registration and transfers of Debentures
(the "DEBENTURE REGISTER"). All overdue accrued and unpaid interest to be paid
hereunder shall entail a late fee at the rate of 12% per annum (or such lower
maximum amount of interest permitted to be charged under applicable law) ("LATE
FEE") which will accrue daily, from the date such interest is due hereunder
through and including the date of payment, except as is set forth in section 5a
of this Debenture, the Company may not prepay any portion of the principal
amount of this Debenture without the prior written consent of the holders."


2.       EVENT OF DEFAULT. Section 3(a)(vii) of the Debenture shall be amended
         and restated as follows:

         (vii) an Underlying Shares Registration Statement shall not have been
         declared effective by the Commission on or prior to November 15, 2004;

3.       SET PRICE OF THE DEBENTURE. Section 4(c)(i) of the Debenture shall be
         amended and restated as follows:

         (c) (i) CONVERSION PRICE. The conversion price in effect on any
         Conversion Date shall be equal to $0.56 (subject to adjustment
         herein)(the "SET PRICE").

4.       MONTHLY REDEMPTION PROCEDURE. Section 5(b) of the Debenture shall be
         amended and restated as follows:

         (b) MONTHLY REDEMPTION. The Company shall redeem (a) $50,000 per month
         on each Monthly Redemption Date, commencing on September 1, 2004 and
         continuing through and until February 1, 2005 and (b) $62,500 per
         month, on each Monthly Redemption Date, beginning on February 1, 2005
         and continuing until the full redemption of this Debenture, plus
         accrued but unpaid interest, the sum of all liquidated damages and any
         other amounts then owing to such Holder in respect of the Debenture.
         The Monthly Redemption Amount due on each Monthly Redemption Date shall
         be payable in cash or Conversion Shares, at the discretion of the
         Company subject to the terms and conditions set forth below. As to any
         Monthly Redemption and upon 20 Trading Days' prior written irrevocable
         notice (the Company may indicate in such notice that the election
         contained in such notice shall continue for later periods until
         revised), in lieu of a cash redemption payment the Company may elect to
         pay 100% of a Monthly Redemption in Conversion Shares based on a
         conversion price equal to 90% of the average of the 20 VWAPs
         immediately prior to the applicable Monthly Redemption Date (subject to
         adjustment for any stock dividend, stock split, stock combination or
         other similar event affecting the Common Stock during such 20 Trading
         Day period) (the "MONTHLY CONVERSION PRICE"); PROVIDED, HOWEVER, that
         the Company may not pay the Monthly Redemption Amount in Conversion
         Shares unless, on the Monthly Redemption Date and during the 20 Trading
         Day period immediately prior thereto, the Equity Conditions have been
         satisfied. The Holders may convert, pursuant to Section 4(a)(i), any

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         principal amount of the Debenture subject to a Monthly Redemption at
         any time prior to the date that the Monthly Redemption Amount and all
         amounts owing thereon are due and paid in full. Any principal amount of
         Debenture converted during any 20 day period until the date the Monthly
         Redemption Amount is paid shall be first applied to the principal
         amount subject to the Monthly Redemption and Holder's payment of the
         Monthly Redemption Amount on such Monthly Redemption Date shall be
         reduced accordingly. The Company covenants and agrees that it will
         honor all Notice of Conversions tendered up until such amounts are paid
         in full.

5.       MONTHLY REDEMPTION DEFINITIONS. Section 6 of the Debenture shall be
         amended to include the following:

                  "MONTHLY REDEMPTION AMOUNT" shall mean (a) $50,000 per month
                  commencing on September 1, 2004 and until February 1, 2005 and
                  (b) $62,500 per month from February 1, 2005 until the full
                  redemption of this Debenture.

                  "MONTHLY REDEMPTION DATE" means the 1st day of each month,
                  commencing on September 1, 2004 and ending upon the full
                  redemption of this Debenture.

6.       OPTIONAL REDEMPTION AMOUNT DEFINITION. The definition of "Optional
         Redemption Amount" set forth in Section 6 of the Debenture is amended
         and restated as follows:

                  "Optional Redemption Amount" shall mean the sum of (a) 100% of
                  the principal amount of the Debenture then outstanding, (b)
                  accrued but unpaid interest and (c) all liquidated damages and
                  other amounts due in respect of the Debentures.

7.       LIQUIDATED DAMAGES/PREPAYMENT PENALTY/WAIVER. The parties hereby agree
         that Midsummer shall accept 600,000 shares of Common Stock as: (a)
         payment in lieu of cash for all accrued and unpaid liquidated damages
         as of the date of this Amendment and including all accrued and unpaid
         liquidated damages owed to Midsummer through and including August 2004
         pursuant to the Purchase Agreement and the Registration Rights
         Agreement, dated as of March 15, 2004 among the Company, Midsummer and
         the Purchasers and attached to the Purchase Agreement as Exhibit B, (b)
         consideration for the amendment of the Debenture to eliminate
         Midsummer's right to a 10% penalty if the Company prepays the
         Debenture; (c) consideration for Midsummer's consent to the Company's
         sale and issuance of the Secured Convertible Term Note and Common Stock
         Purchase Warrant to Laurus Master Fund, Ltd. ("Laurus") pursuant to
         that certain Securities Purchase Agreement between the Company and
         Laurus dated July 12, 2004 (the "Laurus Transaction"); and (d)
         consideration for Midsummer's waiver of all rights and remedies
         accruing as a result of the Laurus Transaction, including without

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         limitation, the right to participate in the Laurus Transaction set
         forth in Section 4.14 of the Purchase Agreement, the covenant against
         future financings set forth in Section 4.7 of the Purchase Agreement
         and the obligation to seek Shareholder Approval prior to effecting any
         issuance that results in an adjustment to the Set Price set forth in
         Section 4.7 of the Purchase Agreement and Section 4(a)(ii)(B) of the
         Debenture.

8.       REGISTRATION OF COMMON STOCK ISSUABLE PURSUANT TO THIS AMENDMENT. All
         shares of Common Stock issuable pursuant to this Amendment shall be
         included in the next registration statement to be filed by the Company
         in August 2004.

9.       EFFECT ON DEBENTURE. Except as expressly set forth above, all of the
         terms and conditions of the Debenture shall continue in full force and
         effect after the execution of this Amendments.

10.      DEFINITIONS. CAPITALIZED TERMS NOT OTHERWISE DEFINED HEREIN HAVE THE
         MEANINGS GIVEN TO SUCH TERMS IN THE PURCHASE AGREEMENT AND THE
         DEBENTURE.

Executed as of July 30, 2004 by the undersigned duly authorized representatives
of the Company and Midsummer:


Island Pacific, Inc.                                 Midsummer Investment Ltd.


By: _________________________                        By: ____________________

Name:                                                Name:

Title:                                               Title:


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